Synthesis 2004(6): 967-969  
DOI: 10.1055/s-2004-815925
PSP
© Georg Thieme Verlag Stuttgart · New York

Preparation of (2-Methyl-propane-2-sulfonylimino) Acetic Acid Ethyl Ester

Marcel Schleusner, Stefan Koep, Markus Günter, Shashi K. Tiwari, Hans-Joachim Gais*
Institut für Organische Chemie der Rheinisch-Westfälischen Technischen Hochschule (RWTH) Aachen, Prof.-Pirlet-Str. 1, 52056 Aachen, Germany
e-Mail: [email protected];
Further Information

Publication History

Received 26 November 2003
Publication Date:
26 January 2004 (online)

Abstract

Synthesis of (2-methyl-propane-2-sulfonylimino) acetic acid ethyl ester from tert-butylsulfonamide, thionyl chloride and ethyl glyoxylate is described. The N-tert-butylsulfonyl imino ester has served as a substitute of the corresponding N-toluenesulfonyl imino ester in allylation reactions.

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18

If desired 5 can be isolated, see ref. [13]

20

A technical 50% solution of ethyl glyoxylate in toluene was concentrated at atmospheric pressure and the residue was distilled to give ethyl glyoxylate as a turbid yellow oil. A second distillation of this material at atmospheric pressure by using a 20 cm Vigreux column at a bath temperature of 160-180 °C furnished ethyl glyoxylate as a yellow fluid, which was used immediately and transferred to the reaction mixture by a syringe.